NPASS Compound

Structure

NPC474733 OpenBabel07101718322D 31 34 0 0 1 0 0 0 0 0999 V2000 -4.7515 -2.4328 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0387 -3.5917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7004 -5.0780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4570 -3.5032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4593 -2.4135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4049 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4133 -3.9190 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0605 -3.3838 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3914 -4.1270 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.1261 -2.7601 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.8171 -1.8090 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.1042 -2.9680 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7734 -2.2248 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 16 1 0 0 0 0 2 16 1 0 0 0 0 7 8 1 0 0 0 0 7 21 1 0 0 0 0 8 22 1 0 0 0 0 9 11 1 0 0 0 0 9 20 1 0 0 0 0 10 12 1 0 0 0 0 10 23 1 0 0 0 0 11 27 1 0 0 0 0 12 28 1 0 0 0 0 13 17 1 0 0 0 0 13 24 1 0 0 0 0 14 19 1 0 0 0 0 14 20 1 0 0 0 0 15 19 2 0 0 0 0 15 25 1 0 0 0 0 16 17 1 0 0 0 0 17 3 1 1 0 0 0 18 4 1 6 0 0 0 18 21 1 0 0 0 0 18 24 1 0 0 0 0 19 27 1 0 0 0 0 20 29 1 1 0 0 0 21 28 1 0 0 0 0 22 26 1 0 0 0 0 22 28 1 1 0 0 0 23 26 1 0 0 0 0 23 27 1 1 0 0 0 24 30 1 1 0 0 0 25 31 2 0 0 0 0 26 25 1 6 0 0 0 27 5 1 1 0 0 0 28 6 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	430.34
Volume:	479.716
LogP:	4.783
LogD:	4.552
LogS:	-5.422
# Rotatable Bonds:	5
TPSA:	57.53
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.581
Synthetic Accessibility Score:	4.731
Fsp3:	0.893
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.758
MDCK Permeability:	1.6670170225552283e-05
Pgp-inhibitor:	0.998
Pgp-substrate:	0.866
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.92
30% Bioavailability (F30%):	0.865

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.373
Plasma Protein Binding (PPB):	97.39070892333984%
Volume Distribution (VD):	1.013
Pgp-substrate:	1.741140365600586%

ADMET: Metabolism

CYP1A2-inhibitor:	0.045
CYP1A2-substrate:	0.577
CYP2C19-inhibitor:	0.11
CYP2C19-substrate:	0.948
CYP2C9-inhibitor:	0.213
CYP2C9-substrate:	0.106
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.126
CYP3A4-inhibitor:	0.593
CYP3A4-substrate:	0.868

ADMET: Excretion

Clearance (CL):	9.471
Half-life (T1/2):	0.18

ADMET: Toxicity

hERG Blockers:	0.606
Human Hepatotoxicity (H-HT):	0.244
Drug-inuced Liver Injury (DILI):	0.08
AMES Toxicity:	0.013
Rat Oral Acute Toxicity:	0.021
Maximum Recommended Daily Dose:	0.175
Skin Sensitization:	0.922
Carcinogencity:	0.19
Eye Corrosion:	0.039
Eye Irritation:	0.248
Respiratory Toxicity:	0.961

Download Data

Data Type	Select
General Info & Identifiers & Properties
Structure MOL file
Source Organisms
Biological Activities
Similar NPs/Drugs

Natural Product: NPC474733

Natural Product ID:	NPC474733
*Common Name:**	Schleicherastatin 6
IUPAC Name:	(3S,8S,9S,10R,13R,14S)-3-hydroxy-17-[(2S,3R,5R)-3-hydroxy-5,6-dimethylheptan-2-yl]-10,13-dimethyl-1,2,3,4,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-7-one
Synonyms:	Schleicherastatin 6
Standard InCHIKey:	PKESXWKAOMUZDM-BBQYQLKJSA-N
Standard InCHI:	InChI=1S/C28H46O3/c1-16(2)17(3)13-24(30)18(4)21-7-8-22-26-23(10-12-28(21,22)6)27(5)11-9-20(29)14-19(27)15-25(26)31/h15-18,20-24,26,29-30H,7-14H2,1-6H3/t17-,18+,20+,21?,22+,23+,24-,26+,27+,28-/m1/s1
SMILES:	O[C@H]1CC[C@]2(C(=CC(=O)[C@@H]3[C@@H]2CC[C@]2([C@H]3CCC2[C@@H]([C@@H](C[C@H](C(C)C)C)O)C)C)C1)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL480674
PubChem CID:	44575194
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001445] Bile acids, alcohols and derivatives [CHEMONTID:0002194] Hydroxy bile acids, alcohols and derivatives [CHEMONTID:0000516] Dihydroxy bile acids, alcohols and derivatives

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO33309	schleichera oleosa	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10650082]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
GI50	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	GI50	=	0.78	ug.mL-1	PMID[531373]

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available in NPASS)

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

● The left chart: Distribution of similarity level between NPC474733 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	160
0.1-0.2	1053
0.2-0.3	4856
0.3-0.4	14277
0.4-0.5	8318
0.5-0.6	6052
0.6-0.7	4794
0.7-0.8	2619
0.8-0.85	377
0.85-0.9	125
0.9-0.95	45
0.95-1	21

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC474732
1.0	High Similarity	NPC474778
1.0	High Similarity	NPC145879
1.0	High Similarity	NPC31564
0.9877	High Similarity	NPC475740
0.9877	High Similarity	NPC58063
0.975	High Similarity	NPC85774
0.975	High Similarity	NPC59453
0.975	High Similarity	NPC221758
0.975	High Similarity	NPC214043
0.9639	High Similarity	NPC186688
0.9639	High Similarity	NPC268406
0.9639	High Similarity	NPC31985
0.9639	High Similarity	NPC1015
0.9639	High Similarity	NPC26959
0.963	High Similarity	NPC469948
0.9524	High Similarity	NPC48010
0.9518	High Similarity	NPC471722
0.9512	High Similarity	NPC222613
0.9512	High Similarity	NPC118648
0.9512	High Similarity	NPC51014
0.9512	High Similarity	NPC475022
0.9506	High Similarity	NPC473246
0.9506	High Similarity	NPC472265
0.95	High Similarity	NPC151519
0.9405	High Similarity	NPC309603
0.9405	High Similarity	NPC473999
0.939	High Similarity	NPC470574
0.9286	High Similarity	NPC328313
0.9286	High Similarity	NPC328539
0.9277	High Similarity	NPC72133
0.9277	High Similarity	NPC155011
0.9268	High Similarity	NPC33913
0.9268	High Similarity	NPC82902
0.9268	High Similarity	NPC161423
0.9268	High Similarity	NPC227064
0.9268	High Similarity	NPC329043
0.9268	High Similarity	NPC237712
0.9268	High Similarity	NPC58841
0.9268	High Similarity	NPC321187
0.925	High Similarity	NPC2482
0.9195	High Similarity	NPC245972
0.9195	High Similarity	NPC196485
0.9186	High Similarity	NPC272746
0.9186	High Similarity	NPC475806
0.9186	High Similarity	NPC473998
0.9176	High Similarity	NPC474245
0.9176	High Similarity	NPC76879
0.9176	High Similarity	NPC32830
0.9176	High Similarity	NPC86319
0.9176	High Similarity	NPC477943
0.9176	High Similarity	NPC275740
0.9176	High Similarity	NPC119416
0.9167	High Similarity	NPC93778
0.9157	High Similarity	NPC474218
0.9157	High Similarity	NPC471224
0.9146	High Similarity	NPC476082
0.9146	High Similarity	NPC278648
0.908	High Similarity	NPC12722
0.908	High Similarity	NPC474736
0.908	High Similarity	NPC475255
0.907	High Similarity	NPC85173
0.907	High Similarity	NPC126993
0.907	High Similarity	NPC191684
0.9059	High Similarity	NPC53911
0.9059	High Similarity	NPC143767
0.9059	High Similarity	NPC131470
0.9048	High Similarity	NPC469994
0.9048	High Similarity	NPC20688
0.9048	High Similarity	NPC327115
0.9012	High Similarity	NPC472478
0.8977	High Similarity	NPC8993
0.8977	High Similarity	NPC111015
0.8966	High Similarity	NPC168027
0.8966	High Similarity	NPC185936
0.8966	High Similarity	NPC131872
0.8941	High Similarity	NPC90652
0.8941	High Similarity	NPC474684
0.8941	High Similarity	NPC141292
0.8941	High Similarity	NPC317590
0.8941	High Similarity	NPC142361
0.8941	High Similarity	NPC136548
0.8929	High Similarity	NPC202868
0.8929	High Similarity	NPC197823
0.8929	High Similarity	NPC474083
0.8902	High Similarity	NPC121984
0.8902	High Similarity	NPC136150
0.8889	High Similarity	NPC108078
0.8876	High Similarity	NPC271195
0.8864	High Similarity	NPC109305
0.8864	High Similarity	NPC250575
0.8864	High Similarity	NPC69454
0.8851	High Similarity	NPC183283
0.8837	High Similarity	NPC470417
0.8837	High Similarity	NPC474677
0.8837	High Similarity	NPC193360
0.8837	High Similarity	NPC292491
0.8837	High Similarity	NPC310752
0.8837	High Similarity	NPC471724
0.8824	High Similarity	NPC94666
0.8824	High Similarity	NPC473168
0.8824	High Similarity	NPC94755
0.881	High Similarity	NPC180834
0.8795	High Similarity	NPC193347
0.8795	High Similarity	NPC320514
0.8765	High Similarity	NPC82635
0.8764	High Similarity	NPC166906
0.875	High Similarity	NPC321381
0.875	High Similarity	NPC63748
0.875	High Similarity	NPC321016
0.875	High Similarity	NPC155304
0.875	High Similarity	NPC233116
0.875	High Similarity	NPC107059
0.8736	High Similarity	NPC326627
0.8736	High Similarity	NPC2983
0.8736	High Similarity	NPC310010
0.8736	High Similarity	NPC474704
0.8736	High Similarity	NPC475921
0.8721	High Similarity	NPC159046
0.8721	High Similarity	NPC233836
0.8721	High Similarity	NPC472484
0.8721	High Similarity	NPC472481
0.8721	High Similarity	NPC472482
0.8721	High Similarity	NPC96496
0.8721	High Similarity	NPC187376
0.8706	High Similarity	NPC29447
0.8675	High Similarity	NPC147066
0.8675	High Similarity	NPC14151
0.8675	High Similarity	NPC477372
0.8667	High Similarity	NPC470016
0.8667	High Similarity	NPC317586
0.8667	High Similarity	NPC469599
0.8667	High Similarity	NPC473170
0.8667	High Similarity	NPC259286
0.8667	High Similarity	NPC472932
0.8659	High Similarity	NPC472490
0.8659	High Similarity	NPC215843
0.8652	High Similarity	NPC474807
0.8652	High Similarity	NPC472930
0.8652	High Similarity	NPC134826
0.8642	High Similarity	NPC155986
0.8642	High Similarity	NPC198968
0.8642	High Similarity	NPC318495
0.8636	High Similarity	NPC69622
0.8636	High Similarity	NPC171441
0.8636	High Similarity	NPC320026
0.8625	High Similarity	NPC230301
0.8625	High Similarity	NPC304309
0.8625	High Similarity	NPC285893
0.8625	High Similarity	NPC288035
0.8625	High Similarity	NPC134847
0.8625	High Similarity	NPC136188
0.8625	High Similarity	NPC22105
0.8625	High Similarity	NPC162742
0.8625	High Similarity	NPC28657
0.8621	High Similarity	NPC242864
0.8621	High Similarity	NPC206060
0.8621	High Similarity	NPC472802
0.8605	High Similarity	NPC89077
0.8605	High Similarity	NPC28252
0.8605	High Similarity	NPC158393
0.8605	High Similarity	NPC55309
0.8588	High Similarity	NPC165064
0.8588	High Similarity	NPC25833
0.8588	High Similarity	NPC144258
0.8587	High Similarity	NPC103051
0.8587	High Similarity	NPC114274
0.8571	High Similarity	NPC328351
0.8571	High Similarity	NPC471463
0.8571	High Similarity	NPC48362
0.8571	High Similarity	NPC96859
0.8571	High Similarity	NPC310989
0.8571	High Similarity	NPC192428
0.8571	High Similarity	NPC260956
0.8571	High Similarity	NPC328162
0.8571	High Similarity	NPC305483
0.8571	High Similarity	NPC212083
0.8571	High Similarity	NPC249954
0.8556	High Similarity	NPC474690
0.8556	High Similarity	NPC292793
0.8554	High Similarity	NPC164999
0.8539	High Similarity	NPC154101
0.8539	High Similarity	NPC19114
0.8539	High Similarity	NPC262870
0.8539	High Similarity	NPC189520
0.8539	High Similarity	NPC86266
0.8539	High Similarity	NPC212301
0.8539	High Similarity	NPC110657
0.8537	High Similarity	NPC477522
0.8537	High Similarity	NPC473943
0.8537	High Similarity	NPC474216
0.8537	High Similarity	NPC87604
0.8523	High Similarity	NPC77168
0.8523	High Similarity	NPC250592
0.8523	High Similarity	NPC77263
0.8523	High Similarity	NPC102414
0.8523	High Similarity	NPC84271
0.8523	High Similarity	NPC472475
0.8523	High Similarity	NPC146554
0.8523	High Similarity	NPC472477

Chemically structural similarity: II. Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC474733 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	142
0.1-0.2	1354
0.2-0.3	3998
0.3-0.4	2543
0.4-0.5	614
0.5-0.6	173
0.6-0.7	106
0.7-0.8	145
0.8-0.85	44
0.85-0.9	22
0.9-0.95	7
0.95-1	2

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.975	High Similarity	NPD4786	Approved
0.95	High Similarity	NPD3667	Approved
0.9405	High Similarity	NPD5328	Approved
0.9277	High Similarity	NPD3618	Phase 1
0.9268	High Similarity	NPD3666	Approved
0.9268	High Similarity	NPD3665	Phase 1
0.9268	High Similarity	NPD3133	Approved
0.9186	High Similarity	NPD6079	Approved
0.8864	High Similarity	NPD4202	Approved
0.8824	High Similarity	NPD5279	Phase 3
0.8795	High Similarity	NPD4223	Phase 3
0.8795	High Similarity	NPD4221	Approved
0.8736	High Similarity	NPD4753	Phase 2
0.8706	High Similarity	NPD5329	Approved
0.8652	High Similarity	NPD6399	Phase 3
0.8625	High Similarity	NPD6942	Approved
0.8625	High Similarity	NPD7339	Approved
0.8588	High Similarity	NPD4197	Approved
0.8588	High Similarity	NPD3668	Phase 3
0.8571	High Similarity	NPD5220	Clinical (unspecified phase)
0.8571	High Similarity	NPD4697	Phase 3
0.8571	High Similarity	NPD5222	Approved
0.8571	High Similarity	NPD5221	Approved
0.8478	Intermediate Similarity	NPD4755	Approved
0.8478	Intermediate Similarity	NPD5173	Approved
0.8391	Intermediate Similarity	NPD5330	Approved
0.8391	Intermediate Similarity	NPD4693	Phase 3
0.8391	Intermediate Similarity	NPD4689	Approved
0.8391	Intermediate Similarity	NPD7334	Approved
0.8391	Intermediate Similarity	NPD6409	Approved
0.8391	Intermediate Similarity	NPD7146	Approved
0.8391	Intermediate Similarity	NPD4138	Approved
0.8391	Intermediate Similarity	NPD5205	Approved
0.8391	Intermediate Similarity	NPD4690	Approved
0.8391	Intermediate Similarity	NPD7521	Approved
0.8391	Intermediate Similarity	NPD4688	Approved
0.8391	Intermediate Similarity	NPD6684	Approved
0.8333	Intermediate Similarity	NPD7515	Phase 2
0.8313	Intermediate Similarity	NPD3617	Approved
0.8298	Intermediate Similarity	NPD5286	Approved
0.8298	Intermediate Similarity	NPD4700	Approved
0.8298	Intermediate Similarity	NPD4696	Approved
0.8298	Intermediate Similarity	NPD5285	Approved
0.8293	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.828	Intermediate Similarity	NPD6083	Phase 2
0.828	Intermediate Similarity	NPD6084	Phase 2
0.8261	Intermediate Similarity	NPD5210	Approved
0.8261	Intermediate Similarity	NPD4629	Approved
0.8256	Intermediate Similarity	NPD4788	Approved
0.8211	Intermediate Similarity	NPD5223	Approved
0.8202	Intermediate Similarity	NPD5737	Approved
0.8202	Intermediate Similarity	NPD6672	Approved
0.8202	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.8202	Intermediate Similarity	NPD6903	Approved
0.8182	Intermediate Similarity	NPD5280	Approved
0.8182	Intermediate Similarity	NPD4694	Approved
0.8182	Intermediate Similarity	NPD5690	Phase 2
0.8125	Intermediate Similarity	NPD4747	Approved
0.8125	Intermediate Similarity	NPD5211	Phase 2
0.8125	Intermediate Similarity	NPD4633	Approved
0.8125	Intermediate Similarity	NPD5224	Approved
0.8125	Intermediate Similarity	NPD5226	Approved
0.8125	Intermediate Similarity	NPD5225	Approved
0.8118	Intermediate Similarity	NPD4695	Discontinued
0.8068	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.8061	Intermediate Similarity	NPD6402	Approved
0.8061	Intermediate Similarity	NPD5739	Approved
0.8061	Intermediate Similarity	NPD7128	Approved
0.8061	Intermediate Similarity	NPD6675	Approved
0.8041	Intermediate Similarity	NPD5174	Approved
0.8041	Intermediate Similarity	NPD4754	Approved
0.8041	Intermediate Similarity	NPD5175	Approved
0.8	Intermediate Similarity	NPD4137	Phase 3
0.8	Intermediate Similarity	NPD4195	Approved
0.7978	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7959	Intermediate Similarity	NPD5141	Approved
0.7957	Intermediate Similarity	NPD7748	Approved
0.7907	Intermediate Similarity	NPD7525	Registered
0.7901	Intermediate Similarity	NPD4691	Approved
0.79	Intermediate Similarity	NPD6881	Approved
0.79	Intermediate Similarity	NPD7320	Approved
0.79	Intermediate Similarity	NPD6899	Approved
0.7879	Intermediate Similarity	NPD4768	Approved
0.7879	Intermediate Similarity	NPD4767	Approved
0.7872	Intermediate Similarity	NPD5695	Phase 3
0.7831	Intermediate Similarity	NPD6926	Approved
0.7831	Intermediate Similarity	NPD5733	Approved
0.7831	Intermediate Similarity	NPD6924	Approved
0.7822	Intermediate Similarity	NPD6372	Approved
0.7822	Intermediate Similarity	NPD6373	Approved
0.7812	Intermediate Similarity	NPD5696	Approved
0.7805	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7805	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.78	Intermediate Similarity	NPD5701	Approved
0.78	Intermediate Similarity	NPD5697	Approved
0.7778	Intermediate Similarity	NPD4519	Discontinued
0.7778	Intermediate Similarity	NPD4623	Approved
0.7745	Intermediate Similarity	NPD7102	Approved
0.7745	Intermediate Similarity	NPD7290	Approved
0.7745	Intermediate Similarity	NPD6883	Approved
0.7742	Intermediate Similarity	NPD5281	Approved
0.7742	Intermediate Similarity	NPD5284	Approved
0.7723	Intermediate Similarity	NPD4729	Approved
0.7723	Intermediate Similarity	NPD5128	Approved
0.7723	Intermediate Similarity	NPD6011	Approved
0.7723	Intermediate Similarity	NPD4730	Approved
0.7723	Intermediate Similarity	NPD5168	Approved
0.7717	Intermediate Similarity	NPD6904	Approved
0.7717	Intermediate Similarity	NPD6673	Approved
0.7717	Intermediate Similarity	NPD6080	Approved
0.7708	Intermediate Similarity	NPD7902	Approved
0.767	Intermediate Similarity	NPD6869	Approved
0.767	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.767	Intermediate Similarity	NPD6650	Approved
0.767	Intermediate Similarity	NPD6617	Approved
0.767	Intermediate Similarity	NPD8130	Phase 1
0.767	Intermediate Similarity	NPD6649	Approved
0.767	Intermediate Similarity	NPD6847	Approved
0.7647	Intermediate Similarity	NPD6933	Approved
0.7647	Intermediate Similarity	NPD6012	Approved
0.7647	Intermediate Similarity	NPD6014	Approved
0.7647	Intermediate Similarity	NPD6013	Approved
0.7634	Intermediate Similarity	NPD4096	Approved
0.7629	Intermediate Similarity	NPD7638	Approved
0.7624	Intermediate Similarity	NPD6412	Phase 2
0.7619	Intermediate Similarity	NPD4058	Approved
0.7619	Intermediate Similarity	NPD4784	Approved
0.7619	Intermediate Similarity	NPD4687	Approved
0.7619	Intermediate Similarity	NPD4785	Approved
0.7614	Intermediate Similarity	NPD4692	Approved
0.7614	Intermediate Similarity	NPD4139	Approved
0.7609	Intermediate Similarity	NPD4518	Approved
0.7609	Intermediate Similarity	NPD5208	Approved
0.7596	Intermediate Similarity	NPD6882	Approved
0.7596	Intermediate Similarity	NPD8297	Approved
0.759	Intermediate Similarity	NPD7150	Approved
0.759	Intermediate Similarity	NPD4243	Approved
0.759	Intermediate Similarity	NPD5276	Approved
0.759	Intermediate Similarity	NPD7151	Approved
0.759	Intermediate Similarity	NPD7152	Approved
0.7582	Intermediate Similarity	NPD6098	Approved
0.7573	Intermediate Similarity	NPD5135	Approved
0.7573	Intermediate Similarity	NPD5249	Phase 3
0.7573	Intermediate Similarity	NPD5248	Approved
0.7573	Intermediate Similarity	NPD5250	Approved
0.7573	Intermediate Similarity	NPD5251	Approved
0.7573	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7573	Intermediate Similarity	NPD4634	Approved
0.7573	Intermediate Similarity	NPD5169	Approved
0.7573	Intermediate Similarity	NPD5247	Approved
0.7561	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD6923	Approved
0.7561	Intermediate Similarity	NPD6922	Approved
0.7551	Intermediate Similarity	NPD7639	Approved
0.7551	Intermediate Similarity	NPD7640	Approved
0.7527	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5215	Approved
0.75	Intermediate Similarity	NPD5127	Approved
0.75	Intermediate Similarity	NPD3171	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5217	Approved
0.75	Intermediate Similarity	NPD5216	Approved
0.7477	Intermediate Similarity	NPD7115	Discovery
0.7474	Intermediate Similarity	NPD5133	Approved
0.747	Intermediate Similarity	NPD4789	Approved
0.747	Intermediate Similarity	NPD4244	Approved
0.747	Intermediate Similarity	NPD4245	Approved
0.747	Intermediate Similarity	NPD7143	Approved
0.747	Intermediate Similarity	NPD7144	Approved
0.7439	Intermediate Similarity	NPD3621	Clinical (unspecified phase)
0.7412	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD7900	Approved
0.7386	Intermediate Similarity	NPD6929	Approved
0.7386	Intermediate Similarity	NPD7645	Phase 2
0.7383	Intermediate Similarity	NPD6868	Approved
0.7368	Intermediate Similarity	NPD6050	Approved
0.7368	Intermediate Similarity	NPD8035	Phase 2
0.7368	Intermediate Similarity	NPD8034	Phase 2
0.7368	Intermediate Similarity	NPD5693	Phase 1
0.7358	Intermediate Similarity	NPD4632	Approved
0.7353	Intermediate Similarity	NPD6008	Approved
0.7349	Intermediate Similarity	NPD3698	Phase 2
0.7303	Intermediate Similarity	NPD8259	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD6931	Approved
0.7303	Intermediate Similarity	NPD6930	Phase 2
0.7303	Intermediate Similarity	NPD4748	Discontinued
0.729	Intermediate Similarity	NPD5167	Approved
0.7273	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD5290	Discontinued
0.7263	Intermediate Similarity	NPD5207	Approved
0.7263	Intermediate Similarity	NPD5692	Phase 3
0.7248	Intermediate Similarity	NPD6335	Approved
0.7241	Intermediate Similarity	NPD6117	Approved
0.7229	Intermediate Similarity	NPD5360	Phase 3
0.7229	Intermediate Similarity	NPD5361	Clinical (unspecified phase)
0.7228	Intermediate Similarity	NPD5091	Approved
0.7222	Intermediate Similarity	NPD6274	Approved

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data